title: Palladium-catalyzed, stereoselective, cyclizative alkenylboration of carbon-carbon double bonds through activation of a boron-chlorine bond.
abstract: Palladium-catalyzed alkenylboration of carbon-carbon double bonds has been achieved using the reaction of chloro(diisopropylamino)boryl ethers of homoallylic alcohols with alkenylzirconium reagents. The reaction may proceed through an initial oxidative addition of the B-Cl bond, intramolecular insertion of the C═C bond into the B-Pd bond, transmetalation from the alkenylzirconium reagent, and reductive elimination of the products. The cyclization proceeds with high diastereoselectivity for the formation of cis-3,5- or trans-3,4-disubstituted-1,2-oxaborolane products. Cross-coupling of the resultant products with aryl iodides proceeds with retention of configuration at the boron-bound secondary carbon atom.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.
authors.forename: Masaki
authors.initials: M
authors.lastname: Daini
authors.forename: Michinori
authors.initials: M
authors.lastname: Suginome
mesh_terms: D001895:Boron / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D002712:Chlorides; D010165:Palladium; D001895:Boron